Diethyl Ether → HCID 89440465, compound

Temperature

120 °C

To a vial is added 5-bromonicotinaldehyde (300 mg, 1.61 mmol) and ethanesulfonamide (220 mg, 2.02 mmol) in 6 ml of toluene, followed by the addition of titanium(IV) isopropoxide (1 ml, 3.23 mmol). The reaction mixture is stirred at 120° C. for 6 hours. The reaction mixture is concentrated. The residue is dissolved in 5 ml of THF and is cooled to −40° C., methylmagnesium bromide, 3M in ether (1.6 ml, 4.84 mmol) is added dropwise. The reaction mixture is warm up and stirred at room temperature for 18 hours. The reaction mixture is diluted with EtOAc, washed with saturated NH4Cl, (aq.) brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 130 mg of ethanesulfonic acid [1-(5-bromo-pyridin-3-yl)-ethyl]-amide.

1. concentrationThe reaction mixture is concentrated
2. dissolutionThe residue is dissolved in 5 ml of THF
3. temperatureis cooled to −40° C.
4. temperatureThe reaction mixture is warm up
5. stirringstirred at room temperature for 18 hours
6. washwashed with saturated NH4Cl, (aq.) brine
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto give the crude product
11. customPurification by the flash column chromatography

ORD record

ord-058c3c68f2b54d20bb4d5916bc26e904

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181272B2